Azobisisobutyronitrile → tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate

Participants

Reaction Conditions

Reaction Steps

27.4 g (0.1 mol) of tert-butyl 2-cyclopentyl-2-(4-methyl-phenyl)-acetate are dissolved in 200 ml of carbon tetrachloride and the solution is heated to boiling. After addition of 0.82 g of azobisisobutyronitrile, 18.7 g (0.105 mol) of N-bromosuccinimide are added in portions and the mixture is then refluxed for 1 h, cooled to 0° C. and filtered off from the succinimide. After concentration of the filtrate the product precipitates. It is washed with petroleum ether (40:60) and dried. Yield: 20 g (57% of theory) Solidification point 73°-76° C.

Provenance & Evidence